EP0846136B1 - Verfahren zur herstellung von auf cashewnussschalenoel basierenden polymeren - Google Patents

Verfahren zur herstellung von auf cashewnussschalenoel basierenden polymeren Download PDF

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Publication number
EP0846136B1
EP0846136B1 EP96927951A EP96927951A EP0846136B1 EP 0846136 B1 EP0846136 B1 EP 0846136B1 EP 96927951 A EP96927951 A EP 96927951A EP 96927951 A EP96927951 A EP 96927951A EP 0846136 B1 EP0846136 B1 EP 0846136B1
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EP
European Patent Office
Prior art keywords
cnso
manufacturing
polyisocyanate
mixture
cashew
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP96927951A
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English (en)
French (fr)
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EP0846136A1 (de
Inventor
Martin Ernst Stielau
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
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Individual
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Publication date
Priority claimed from PT10176195A external-priority patent/PT101761B/pt
Priority claimed from PT10186396A external-priority patent/PT101863A/pt
Application filed by Individual filed Critical Individual
Publication of EP0846136A1 publication Critical patent/EP0846136A1/de
Application granted granted Critical
Publication of EP0846136B1 publication Critical patent/EP0846136B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/54—Polycondensates of aldehydes
    • C08G18/542—Polycondensates of aldehydes with phenols

Definitions

  • the present invention relates to polymers based on cashew shell (from now HCNC) which together with di- and / or polyisocyanates can constitute multiple molecular networks.
  • HCNC is a by-product of the food industry of cashew nut preparation.
  • This liquid located under the shell of the nut and which is released at opening time, is a 9: 1 mixture of a fatty acid (anacardic acid, which carries a phenolic group to the benzene ring) and a diphenol (Cardol), both with side chains with 15 carbon atoms and 27 of hydrogen and one to three double bonds.
  • a fatty acid anacardic acid, which carries a phenolic group to the benzene ring
  • Cardol diphenol
  • Showa's Japanese Patent No. 33-27,905 dated 1.10.1958 teaches a new application for this product by reacting it with di-and / or polyisocyanates.
  • This polyurethane manufacturing method thanks to a reaction between HCNC and a polyisocyanate, shows the possibility of making dimerize HCNC in the presence of polymerization catalyst and at temperatures up to 140 ° C.
  • the result of this preparation is a product very viscous, which can be used in a practical way with isocyanates, must be washed and dried beforehand.
  • German patent n ° 2152 606 of 22.10.71 of Bayer AG teaches as part of an internal plasticization process of an epoxy resin, that phenolic groups can be used to block temporarily NCO groups of excess polyisocyantes of prepolymers. After a subsequent reaction, in which tertiary amines take the place of the phenols, these remaining free in the product.
  • the present invention shows how polymers based on HCNC can be made in a simpler way, and products with NCO groupings blocked in a cleaner way by linking groupings phenolics released to an available aldehyde.
  • We can, thanks to the procedures invented, make products as varied as: rigid foams, elastomers, thermoplastic rubbers or one-component binders without solvents.
  • the first level is always interesting when the expansion of a product is desired.
  • a polyisocyanate at three levels, achieve a rigid foam of excellent quality.
  • Different polymerizable components are obtained either by simply heating the HCNC or by the following preparation. Add a small amount of dilute sulfuric acid to the oil and heat. Around 130 ° C the CO 2 of the carboxyl escapes, by heating more, one progresses in concentration and dimerization. By adding a polyisocyanate, more or less crosslinked products are obtained.
  • HCNC is heated with a small amount of acid sulfuric diluted to 180 ° C, allowed to cool to 120 ° C and added a equivalent amount in TDI. This mixture is kept at a temperature of 80 ° C. until there is no more free isocyanate.
  • This second component is for example a mixture of HCNC and Furfural, which had been previously heated with a small amount of triethylamine and allowed to cool to room temperature. (It has been discovered, that a such mixture remains stable at this temperature).
  • the amount of Furfural in the second mixture corresponds to the total amount of HCNC decarboxylated and if the mixture is heated the first preparation with that of the second at a temperature above 150 ° C, then the initially blocked NCO groups are released and react with the COOH of the second preparation, the phenolic groups react with Furfural, and give a very shiny, hard product but still flexible.
  • Preparation with blocked isocyanate may - patent-like Bayer - be used to make epoxy resins flexible or, by heating, make elastic products.
  • HCNC and Furfural can - as explained the following example - serve as a component for the manufacture of a rigid foam, under the condition that an isocyanate can react beforehand with the OH of HCNC carboxyls.
  • HCNC 100 g of HCNC are mixed with 28 g of Furfural and the mixture is heated to 150 ° C. From a rapid mixing with 32 g of TDI or 49 g of MDI results: expansion, crosslinking and hardening. The resulting rigid foam obtains its final characteristics after a few days.
  • a first mixture of 34 g of HNCN and 19 g of Furfural will be heated while stirring it to a temperature of 150 ° C.
  • a second mixture consisting of 34 g of HNCN and 0.68 g sulfuric acid (50%) is heated to a temperature of 170 ° C, cooled to 110 ° C and supplemented with 7 g of TDI. Stir slowly under nitrogen for 4 hours at a temperature of 70 ° C and allowed to cool.
  • HNCN 100 g of HNCN are heated to a temperature of 300 ° C. After cooling to room temperature, 40 g of MDI are added and mixed well. After an exothermic reaction, a duromer of good resistance is obtained mechanical and chemical.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compounds Of Unknown Constitution (AREA)

Claims (5)

  1. Verfahren zur Herstellung einer Kunststoffkomponente auf Basis von Cashewnußschalenöl (CNSÖ) dessen Phenolgruppen vorübergehend durch die NCO-Gruppen eines Di-und/oder Polyisocyanates blockiert worden sind, dadurch gekennzeichnet, daß:
    a) das CNSÖ z.B.mittels des Zusatzes einer kleinen Menge verdünnter Schwefelsäure vollständig decarboxylisiert worden ist.
    b) Vor der Dimerisierung durch Erhitzen eine äquivalente Menge an TDI hinzugefügt worden ist.
    c) Erneut, bis zur kompletten Blockierung des Isocyanates erhitzt wurde.
  2. Verfahren zur Herstellung einer Kunststoffkomponente auf Basis von CNSÖ welches mit einem Aldehyd, vorzugsweise Furfural, präkondensiert woden und dadurch dadurch gekennzeichnet ist, daß:
    a) das CNSÖ mit einer kleinen Menge Triethylamin bis etwa 170°C erhitzt wird.
    b) Eine äquivalente Menge von einem Aldehyd (vorzugsweise Furfural) hinzugegeben wird.
    c) Erneut bis zum Beginn einer Kondensation erhitzt wird.
  3. Verfahren gemäß 1 und 2 dadurch gekennzeicnet daß äquivalente Mengen der Komponente gemäß 2 vermischt werden.
  4. Verfahren zur Herstellung eines Polymers dadurch gekennzeichnet daß ein Di-und/oder Polyisocyanat mit einem CNSÖ reagiert, welches zuvor-z.B. durch den Zusatz einer kleinen Menge von Schwefelsäure und anschließender Eritzung auf über 140°C - vollständig decarboxylisiert worden ist.
  5. Verfahren zur Herstellung von Hartschaum, dadurch gekennzeichnet, daß ein Di-und/order Polyisocyanat mit CNSÖ reagiert.
EP96927951A 1995-08-21 1996-08-20 Verfahren zur herstellung von auf cashewnussschalenoel basierenden polymeren Expired - Lifetime EP0846136B1 (de)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
PT10176195 1995-08-21
PT10176195A PT101761B (pt) 1995-08-21 1995-08-21 Processo de fabrico de novos polimeros a base de oleo da casca de castanha de caju
PT10186396A PT101863A (pt) 1996-04-04 1996-04-04 Processo de fabrico de uma espuma rigida a base de oleo da casca da castanha de caju
PT10186396 1996-04-04
PCT/PT1996/000007 WO1997007150A1 (fr) 1995-08-21 1996-08-20 Procede de fabrication de nouveaux polymeres a base d'huile de coquille de noix de cajou et les produits qui en resultent

Publications (2)

Publication Number Publication Date
EP0846136A1 EP0846136A1 (de) 1998-06-10
EP0846136B1 true EP0846136B1 (de) 2001-01-24

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Application Number Title Priority Date Filing Date
EP96927951A Expired - Lifetime EP0846136B1 (de) 1995-08-21 1996-08-20 Verfahren zur herstellung von auf cashewnussschalenoel basierenden polymeren

Country Status (10)

Country Link
US (1) US6051623A (de)
EP (1) EP0846136B1 (de)
JP (1) JPH11512122A (de)
AP (1) AP9801213A0 (de)
AT (1) ATE198899T1 (de)
AU (1) AU704532B2 (de)
BR (1) BR9610395A (de)
DE (1) DE69611679D1 (de)
OA (1) OA10667A (de)
WO (1) WO1997007150A1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015077927A1 (en) * 2013-11-27 2015-06-04 Dow Global Technologies Llc Curable polyurethane coating composition and method of preparing the same

Families Citing this family (19)

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US7595094B2 (en) 1998-09-17 2009-09-29 Urethane Soy Systems, Co. Vegetable oil-based coating and method for application
US6962636B2 (en) 1998-09-17 2005-11-08 Urethane Soy Systems Company, Inc. Method of producing a bio-based carpet material
US7063877B2 (en) 1998-09-17 2006-06-20 Urethane Soy Systems Company, Inc. Bio-based carpet material
US6180686B1 (en) 1998-09-17 2001-01-30 Thomas M. Kurth Cellular plastic material
US20030191274A1 (en) 2001-10-10 2003-10-09 Kurth Thomas M. Oxylated vegetable-based polyol having increased functionality and urethane material formed using the polyol
US20020058774A1 (en) 2000-09-06 2002-05-16 Kurth Thomas M. Transesterified polyol having selectable and increased functionality and urethane material products formed using the polyol
US6979477B2 (en) 2000-09-06 2005-12-27 Urethane Soy Systems Company Vegetable oil-based coating and method for application
DE10004427A1 (de) * 2000-02-02 2001-10-04 Martin Stielau Verfahren zur Herstellung von Polyurethan
WO2001070842A2 (en) * 2000-03-20 2001-09-27 Kt Holdings, Llc Polyurethane foams
BRPI0418851A (pt) * 2004-06-30 2007-11-20 Council Scient Ind Res processo para a preparação de um poliol de poliuretano
US7244772B2 (en) * 2004-06-30 2007-07-17 Council Of Scientific And Industrial Research Process for preparing polyurethane polyol and rigid foams therefrom
CN101218272A (zh) 2005-03-03 2008-07-09 南达科他大豆处理机有限公司 采用氧化方法从植物油衍生的新型多元醇
US8048979B2 (en) * 2005-12-30 2011-11-01 Council Of Scientific And Industrial Research Process for synthesis of telechelic urethane acrylate UV curable pre-polymeric materials
US7828991B2 (en) 2006-12-08 2010-11-09 Bayer Materialscience Llc Polyether polyols based on cashew nutshell liquid and flexible foams
TR201903021T4 (tr) * 2013-06-25 2019-03-21 Covestro Llc Geliştirilmiş kaplama yapışmasına sahip ürünlerin üretimine yönelik poliüretan pultruzyon formülasyonları ve bunlardan üretilen ürünler.
JP2015117275A (ja) * 2013-12-17 2015-06-25 住化バイエルウレタン株式会社 ポリウレタン樹脂用原料としてのカシューナッツ殻液の使用
JP6656796B2 (ja) * 2014-08-27 2020-03-04 コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ ポリイソシアヌレートフォーム原料としてのカシューナッツ殻液の使用
JP6683696B2 (ja) 2014-11-05 2020-04-22 ダウ グローバル テクノロジーズ エルエルシー 難燃性ポリオール
JP2023092020A (ja) * 2021-12-21 2023-07-03 株式会社イノアックコーポレーション ポリウレタンフォームとその製造方法及びシール材

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US4301254A (en) * 1980-03-14 1981-11-17 Blount David H Process for the production of poly(aldehyde aminosilicon acid) resinous products and foams
JPS604840A (ja) * 1983-06-22 1985-01-11 Agency Of Ind Science & Technol 流体検出装置
JPS60212453A (ja) * 1984-04-09 1985-10-24 Kanegafuchi Chem Ind Co Ltd 硬化性樹脂組成物
JPH06102770B2 (ja) * 1988-02-10 1994-12-14 斎藤株式会社 カシュー樹脂変性ポリウレタン樹脂塗料の製造方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015077927A1 (en) * 2013-11-27 2015-06-04 Dow Global Technologies Llc Curable polyurethane coating composition and method of preparing the same

Also Published As

Publication number Publication date
ATE198899T1 (de) 2001-02-15
WO1997007150A1 (fr) 1997-02-27
OA10667A (fr) 2002-09-25
JPH11512122A (ja) 1999-10-19
DE69611679D1 (de) 2001-03-01
US6051623A (en) 2000-04-18
AU6758396A (en) 1997-03-12
BR9610395A (pt) 2000-05-09
AU704532B2 (en) 1999-04-29
AP9801213A0 (en) 1998-03-31
EP0846136A1 (de) 1998-06-10

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